Reaction engineering and photophysical studies of fully enriched C-vinyl-1,2,3-triazoles

For the first time, an enolate-mediated organocatalytic fluorogenic formal [3 + 2]-cycloaddition of (E)-1,4-diarylbut-3-en-1-ones and aryl azides is reported. The mild metal-free catalytic conditions of this reaction allowed us to synthesize a library of pure fluorescent coumarin-triazole dyes. It i...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2019-11, Vol.6 (21), p.3620-3628
Main Authors: Reddy, G Surendra, Ramachary, Dhevalapally B
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical synthesis
Coumarin
Crystal structure
Crystallography
Cycloaddition
Fluorescence
NMR
Nuclear magnetic resonance
Organic chemistry
Selectivity
Substrates
Triazoles
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Summary:For the first time, an enolate-mediated organocatalytic fluorogenic formal [3 + 2]-cycloaddition of (E)-1,4-diarylbut-3-en-1-ones and aryl azides is reported. The mild metal-free catalytic conditions of this reaction allowed us to synthesize a library of pure fluorescent coumarin-triazole dyes. It is an efficient formal [3 + 2]-cycloaddition for the synthesis of fully decorated C-vinyl-1,2,3-triazoles with excellent outcomes with reference to the rate, yield, selectivity, operation simplicity, substrate scope, and photophysical applications.
ISSN:2052-4110
2052-4110
DOI:10.1039/c9qo00864k